This application is a 371 of PCT/EP00/04300, published May 12, 2000.
The present invention relates to novel processes for preparing methoxyimino-acetamides.
A process for preparing N-methyl-[2-(2-hydroxy)phenyl]-2-methoxyimino-acetamide has already been described (cf. EP 0 398 692 A2). However, the compounds prepared by this process are only obtainable in moderate yields.
It has now been found that according to process part 1) compounds of the formula (I) 
in which
R1, R2, R3 and R4 are identical or different and independently of one another each represents hydrogen, halogen, cyano, nitro, in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl,
R5 represents substituted or unsubstituted alkyl,
R6 represents hydrogen, substituted or unsubstituted alkyl,
are obtained when
A) according to process step 2), compounds of the formula (IV), 
xe2x80x83in which
R1, R2, R3 and R4 are as defined above,
are reacted, in the presence of an acid or an acidic ion exchanger, with an alcohol of the formula (V),
R7xe2x80x94OHxe2x80x83xe2x80x83(V)
xe2x80x83in which
R7 represents substituted or unsubstituted alkyl,
and with a carbonyl compound, which binds the hydroxylammonium chloride eliminated in the reaction forming an oxime, to give compounds of the formula (VI), 
xe2x80x83in which
R1, R2, R3, R4 and R7 are as defined above,
and the resulting compounds of the formula (VI) are either
a) according to process step 3), reacted with a hydroxylammonium salt, if appropriate in the presence of a diluent and if appropriate in the presence of an acid or an acid acceptor, to give compounds of the formula (VII), 
xe2x80x83in which
R1, R2, R3, R4 and R7 are as defined above,
and the resulting compounds of the formula (VII) are, according to process step 4), reacted with an alkylating agent of the formula (VIII),
R5xe2x80x94Xxe2x80x83xe2x80x83(VIII)
xe2x80x83in which
R5 is as defined above and
X represents halogen, xe2x80x94Oxe2x80x94COxe2x80x94OR5xe2x80x94 or xe2x80x94Oxe2x80x94SO2xe2x80x94Oxe2x80x94R5, where R5 is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of a base,
or
b) are, according to process step 5), reacted with an alkoxyamine of the formula (IX),
R5xe2x80x94Oxe2x80x94NH2xe2x80x83xe2x80x83(IX)
xe2x80x83in which
R5 is as defined above,
xe2x80x94 or an acid addition complex thereofxe2x80x94, if appropriate in the presence of a diluent and if appropriate in the presence of an acid or an acid acceptor,
or when
B) according to process step 6), compounds of the formula (IV), 
xe2x80x83in which
R1, R2, R3 and R4 are as defined above,
are reacted with an alkoxyamine of the formula (IX),
R5xe2x80x94Oxe2x80x94NH2xe2x80x83xe2x80x83(IX)
xe2x80x83in which
R5 is as defined above,
xe2x80x94 or an acid addition complex thereofxe2x80x94if appropriate in the presence of a diluent and if appropriate in the presence of an acid,
or when
C) according to process step 7), compounds of formula (IV), 
xe2x80x83in which
R1, R2, R3 and R4 are as defined above,
are reacted, in the presence of an acid or an acidic ion exchanger, with an alcohol of the formula (V),
R7xe2x80x94OHxe2x80x83xe2x80x83(V)
in which R7 is as defined above,
if appropriate with addition of a hydroxylammonium salt, and the resulting compounds of the formula (VII), 
xe2x80x83in which
R1, R2, R3, R4 and R7 are as defined above,
are reacted according to process step 4),
or when
D) according to process step 8), compounds of the formula (X), 
xe2x80x83in which
R1, R2, R3, R4 and R5 are as defined above,
are reacted, in the presence of an acid or an acidic ion exchanger, with an alcohol of the formula (V),
R7xe2x80x94OHxe2x80x83xe2x80x83(V)
xe2x80x83in which R7 is as defined above, if appropriate in the presence of a carbonyl compound which binds the hydroxylammonium chloride eliminated in the reaction forming an oxime,
and the compounds of the formula (II) obtained according to proceses A)-D), 
xe2x80x83in which
R1, R2, R3, R4 and R5 are as defined above and
R7 represents unsubstituted or substituted alkyl,
are, if appropriate without intermediate isolation of the compounds of the formula (II) (one-pot process),
reacted according to process step 1) with an alkylamine of the formula (III),
R6xe2x80x94NH2xe2x80x83xe2x80x83(III)
in which R6 is as defined above, if appropriate in the presence of a diluent.
Moreover, it has been found that, according to process part 2), compounds of the formula (XI), 
in which
Z represents unsubstituted or substituted cycloalkyl, aryl or heterocyclyl,
Q represents oxygen or sulphur,
Y represents halogen and
R1, R2, R3, R4, R5 and R7 are as defined above,
are obtained when compounds of the formula (I) are reacted according to the novel process part 1), and these compounds (I) are either
E) according to process step 9) reacted with pyrimidine derivatives of the formula (XII), 
xe2x80x83in which
T1 and T2 are identical or different and represent halogen or xe2x80x94SO2xe2x80x94R8, where R8 is alkyl, aryl or benzyl, and
Y is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of a base, and the resulting compounds of the formula (XIII), 
xe2x80x83in which
T2, Y, R1, R2, R3, R4, R5 and R7 are as defined above,
are reacted, according to process step 10), with a cyclic compound of the general formula (XIV),
Zxe2x80x94Qxe2x80x94Hxe2x80x83xe2x80x83(XIV)
xe2x80x83in which
Z and Q are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor and if appropriate in the presence of a catalyst,
or
F) are reacted according to process step 11) with compounds of the formula (XV), 
in which
Z, Q, T1 and Y are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of a base.
Furthermore, it has been found that the Z-isomeric compounds of the formula (XI) are isomerized to E-isomeric compounds of the formula (XI) when Z isomers or E/Z isomer mixtures of the compounds of the formula (XI) are treated with acids, if appropriate in a diluent. The isomerization affords the E isomers in good yields.
Furthermore, it has been found that the Z-isomeric compounds of the formula (XIII) are isomerized to E-isomeric compounds of the formula (XIII) when Z isomers or E/Z isomer mixtures of the compounds of the formula (XIII) are treated with acids, if appropriate in a diluent. The isomerization affords the E isomers in good yields.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, are, including in combination with heteroatoms, such as, for example, in alkoxy, alkylthio or alkylamino, in each case straight-chain or branched having in particular 4 carbon atoms.
Aryl denotes aromatic, mono- or polycyclic hydrocarbons rings, such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
Halogen generally denotes fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine. Heterocyclyl denotes saturated or unsaturated, and also aromatic, cyclic compounds in which at least one ring member is a heteroatom, i.e. an atom different from carbon. If the ring contains a plurality of heteroatoms, these can be identical or different. Preferred heteroatoms are oxygen, nitrogen or sulphur. If appropriate, the cyclic compounds form a polycyclic ring system together with further carbocyclic or heterocyclic fused-on or bridged rings. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Cycloalkyl denotes saturated carbocyclic compounds which may, if appropriate, form a polycyclic ring system with further carbocyclic, fused-on or bridged rings.
Halogenoalkyl denotes partially or fully halogenated alkyl. In the case of polyhalogenated halogenoalkyl, the halogen atoms can be identical or different. Preferred halogen atoms are fluorine and chlorine and in particular fluorine. If the halogenoalkyl also carries other substituents, the maximum number of halogen atoms possible is reduced to the remaining free valencies.
The compounds according to the invention can, if appropriate, be present as mixtures of different possible isomeric forms, in particular of stereoisomers, such as, for example E and Z. What is claimed are both the E and the Z isomers, and any mixtures of these isomers.
In general, Z represents in particular:
cycloalkyl having 3 to 7 carbon atoms which is in each case optionally mono- to disubstituted by halogen, alkyl or hydroxyl;
heterocyclyl having 3 to 7 ring members which is optionally substituted by alkyl having 1 to 4 carbon atoms;
or phenyl or naphthyl, each of which is optionally mono- to tetrasubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 8 carbon atoms;
in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkylaminocarbonyloxy, alkenylcarbonyl or alkinylcarbonyl having 1 to 6 carbon atoms in the respective hydrocarbon chains;
cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms;
in each case doubly attached alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms, each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, oxo, methyl, trifluoromethyl and ethyl;
or a grouping 
xe2x80x83in which
A1 represents hydrogen, hydroxyl or alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
A2 represents hydroxyl, amino, methylamino, phenyl, benzyl or represents in each case optionally cyano-, hydroxyl-, alkoxy-, alkylthio-, alkylamino-, dialkylamino- or phenyl-substituted alkyl or alkoxy having 1 to 4 carbon atoms, or represents alkenyloxy or alkinyloxy having in each case 2 to 4 carbon atoms,
and phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl or phenylalkyl, phenylalkyloxy, phenylalkylthio, or heterocyclylalkyl having in each case 1 to 3 carbon atoms in the respective alkyl moieties, each of which is optionally mono- to trisubstituted in the ring moiety by halogen and/or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms.
Generally, R5 represents in particular methyl or ethyl.
Generally, R6 represents in particular hydrogen or methyl.
Generally, R7 represents in particular methyl.
Generally, Q represents in particular oxygen or sulphur.
Generally, Y represents in particular fluorine, chlorine, bromine or iodine.
Generally, T1 represents in particular fluorine or chlorine.
Generally, T2 represents in particular fluorine or chlorine.
In general, R1, R2, R3 and R4 are identical or different and independently of one another each represents in particular hydrogen, halogen, cyano, nitro, or alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms and being in each case optionally substituted by 1 to 5 halogen atoms.
Preference is given to inventions in which Z represents cyclopentyl or cyclohexyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, methyl, ethyl or hydroxyl;
represents optionally methyl- or ethyl-substituted thienyl, pyridyl or furyl;
or represents phenyl or naphthyl, each of which is optionally mono- to tetrasubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
fluorine, chlorine, bromine, iodine, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3-, 4-(2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-, 4-, 5-(2-methylpentyl), 1-, 2-, 3-(3-methylpentyl), 2-ethylbutyl, 1-, 3-, 4-(2,2-dimethylbutyl), 1-, 2-(2,3-dimethylbutyl), hydroxymethyl, hydroxyethyl, 3-oxobutyl, methoxymethyl, dimethoxymethyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, vinyl, allyl, 2-methylallyl, propene-1-yl, crotonyl, propargyl, vinyloxy, allyloxy, 2-methylallyloxy, propene-1-yloxy, crotonyloxy, propargyloxy;
trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, benzylaminocarbonyl, acryloyl, propioloyl, cyclopentyl, cyclohexyl,
in each case doubly attached propanediyl, ethyleneoxy, methylenedioxy, ethylenedioxy, each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, oxo, methyl and trifluoromethyl,
or a grouping 
xe2x80x83where
A1 represents hydrogen, methyl or hydroxyl and
A2 represents hydroxyl, methoxy, ethoxy, amino, methylamino, phenyl, benzyl or hydroxyethyl, and
phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, benzyl, phenylethyl, phenylpropyl, benzyloxy, benzylthio, 5,6-dihydro-1,4,2-dioxazin-3-ylmethyl, triazolylmethyl, benzoxazol-2-ylmethyl, 1,3-dioxan-2-yl, benzimidazol-2-yl, dioxol-2-yl, oxadiazolyl, each of which is optionally mono- to trisubstituted in the ring moiety by halogen and/or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms.
Preference is given to compounds in which R5 represents methyl.
Preference is given to compounds in which R6 represents hydrogen or in particular methyl.
Preference is given to compounds in which R7 represents methyl.
Preference is given to compounds in which Q represents sulphur or in particular oxygen.
Preference is given to compounds in which Y represents fluorine or chlorine.
Preference is given to compounds in which R1, R2, R3 and R4 are identical or different and independently of one another each represents hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl.
In a very particularly preferred group of compounds, Z represents optionally substituted phenyl.
In a further very particularly preferred group of compounds
R1 and R3 independently of one another represent methyl and in particular hydrogen and
R2 and R4 represent hydrogen.
Particular preference is given to compounds in which Y represents fluorine.
Particular preference is given to compounds in which Q represents oxygen.
The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and/or the formula (XI) and also correspondingly to the starting materials or intermediates required in each case for the preparation.
The radical definitions given in the respective combinations or preferred combinations of radicals for these individual radicals are, independently of the combination of radicals given in each case, also replaced by any radical definitions of other preferred ranges.
These radical definitions can be combined with each other at will, i.e. including combinations between the given ranges of preferred compounds.
The compound of the formula (XI-1, E-isomer) is novel and inventive and forms also part of the subject-matter of the invention. It can be used by way of example as pesticide. 
The compound of the formula (XI-1, Z-isomer) is novel and inventive and forms also part of the subject-matter of the invention. It can be used by way of example as pesticide. 
The isomerization of the compounds of the formula (XI) is preferably carried out after process steps 10 and 11.
Suitable diluents for carrying out the process according to the invention are, by way of example and by way of preference, alcohols, in particular methanol; ethers, in particular tetrahydrofuran; or alkylnitriles, in particular acetonitrile.
Preferred diluents for carrying out the process step 1 are ethers, in particular tetrahydrofuran; or alcohols, in particular ethanol, preferably methanol.
Preferred diluents for carrying out the process step 2 are alcohols, in particular methanol, pyridine, water or mixtures thereof.
Preferred diluents for carrying out process step 3 are alcohols, in particular methanol; dialkyl ketones, in particular acetone; dialkylformamides, in particular dimethylformamide, pyrrolidone, or dialkylacetamides; in particular dimethylacetamide.
Preferred diluents for carrying out the process step 4 are alkylnitriles, in particular acetonitrile.
Preferred diluents for carrying out the process step 5 are alcohols, in particular methanol, pyridine, water or mixtures thereof.
Preferred diluents for carrying out the process step 6 are alcohols, in particular methanol.
Preferred diluents for carrying out the process step 7 are alcohols, in particular methanol.
Preferred diluents for carrying out the process step 8 are alcohols, in particular methanol.
Preferred diluents for carrying out the process step 9 are alkylnitriles, in particular acetonitrile, dialkyl ketones, in particular acetone, dialkylformamides, in particular dimethylformamide, pyrrolidone, or dialkylacetamides, in particular dimethylacetamide.
Preferred diluents for carrying out the process step 10 are alkylnitriles, in particular acetonitrile, dialkyl ketones, in particular acetone, dialkylformamides, in particular dimethylformamide, pyrrolidone, or dialkylacetamides, in particular dimethylacetamide.
Preferred diluents for carrying out the process step 11 are alkylnitriles, in particular acetonitrile, dialkyl ketones, in particular acetone, dialkylformamides, in particular dimethylformamide, pyrrolidone, or dialkylacetamides, in particular dimethylacetamide.
Suitable diluents for carrying out the isomerization are all inert organic solvents. These preferably include aromatic hydrocarbons, such as for example toluene or xylene, esters, such as, for example, ethyl acetate or n-butylacetate, ethers, such as, for example tert-butyl methyl ether, dioxane, tetrahydrofuran or dimethoxyethane, ketones, such as, for example, acetone, butanone, cyclohexanone or methyl isobutylketone, or alcohols, such as, for example methanol, ethanol, n- or i-propanol, n-, i-, or t- butanol, or mixtures thereof with water.
For the purpose of the invention, acids are relatively highly concentrated acids, in particular mineral acids or hydrogen chloride gas.
The preferred mineral acid is hydrochloric acid, in particular hydrogen chloride gas.
For the isomerization, relatively highly concentrated acids, in particular mineral acids or sulfonic acids, for example and in particular sulfuric acid, methanesulfonic acid, hydrochloric acid and hydrogen chloride gas are employed.
The acidic ion exchangers used in the processes according to the invention are preferably perfluorinated ion exchangers.
The processes according to the invention are, if appropriate, carried out in the presence of a suitable acid acceptor/base. Suitable acid acceptors/bases are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal carbonates, such as, for example, potassium carbonate; alkaline earth metal or alkali metal bicarbonates, such as, for example , potassium bicarbonate; primary amines, such as methylanine, tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU), particularly preferably alkali metal acetates, in particular sodium acetate.
In process step 1, preference is given to using methylamine.
In process step 3, preference is given to using sodium acetate.
In process step 4, preference is given to using potassium bicarbonate.
In process step 5, preference is given to using sodium acetate.
In process step 9, preference is given to using potassium carbonate.
In process step 10, preference is given to using potassium carbonate.
In process step 11, preference is given to using potassium carbonate.
The alkoxyamines used in process step 5 are in particular methoxyamine and/or its hydrochloride salt.
The alkoxyamines used in process step 6 are in particular methoxyamine and/or its hydrochloride salt.
When carrying out the processes according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the processes are carried out in a temperature range of from 0xc2x0 C. to the reflux temperature of the mixture in question, in particular at reflux temperature.
The reactions according to process step 1 are preferably carried out in a temperature range from 0xc2x0 C. to room temperature, in particular at 5-15xc2x0 C.
The reactions according to process step 2 are preferably carried out in a temperature range from room temperature to the reflux temperature of the mixture in question, in particular at reflux temperature.
The reactions according to process step 3 are preferably carried out in a temperature range from room temperature to the reflux temperature of the mixture in question, in particular at room temperature.
The reactions according to process step 4 are preferably carried out in a temperature range from room temperature to the reflux temperature of the mixture in question, in particular at reflux temperature.
The reactions according to process step 5 are preferably carried out in a temperature range from room temperature to the reflux temperature of the mixture in question, in particular at reflux temperature.
The reactions according to process step 6 are preferably carried out in a temperature range from room temperature to the reflux temperature of the mixture in question, in particular at reflux temperature.
The reactions according to process step 7 are preferably carried out in a temperature range from room temperature to the reflux temperature of the mixture in question.
The reactions according to process step 8 are preferably carried out in a temperature range from room temperature to the reflux temperature of the mixture in question.
The reactions according to process step 9 are preferably carried out in a temperature range from room temperature to the reflux temperature of the mixture in question.
The reactions according to process step 10 are preferably carried out in a temperature range from room temperature to the reflux temperature of the mixture in question.
The reactions according to process step 11 are preferably carried out in a temperature range from room temperature to the reflux temperature of the mixture in question.
The reactions of the processes according to the invention are carried out under atmospheric pressure, under elevated or under reduced pressure, preferably under atmospheric pressure.
Preferred carbonyl compounds are dialkyl ketones, in particular acetone, aldehydes or glyoxylic acid.
Preferred alkylating agents are carbonates, in particular dialkyl carbonates, particularly preferably dimethyl carbonate, dialkyl sulphates, in particular dimethyl sulphate, or particularly preferably alkyl halides, in particular methyl chloride.
Preferred pyrimidine derivatives of the formula (XII) in process step 9) are trifluoropyrimidine or fluorodichloropyrimidines, in particular 5-fluoro-4,6-dichloropyrimidine.
Particular preference is given to carrying out process part 1A)a) without intermediate isolation of the compounds of the formulae (VI), (VII) and (II) (one-pot process).
Particular preference is given to carrying out process part 1A)b) without intermediate isolation of the compounds of the formulae (VI) and (II) (one-pot process).
Particular preference is given to carrying out process part 1B) without intermediate isolation of the compounds of the formula (II) (one-pot process)
Particular preference is given to carrying out process part 1C) without intermediate isolation of the compounds of the formula (VII) and (II) (one-pot process).
Particular preference is given to carrying out process part 1D) without intermediate isolation of the compounds of formula (II) (one-pot process).
Particular preference is given to carrying out process part 1 and part 2 without isolation of the intermediate compounds (one-pot process).
The starting materials of the formula (IV) used for carrying out the process steps 2), 6) and 7) are known and can be prepared by known processes (cf. Beilstein, E (II) 17, 462; Mameli, G. 56, 768; Chem. Ber. 35 (1902), 1640-1646; Proc. Indian Acad. Sci. Sect. A (1976) 83A(6), 238-242).
Some of the compounds of the formula (VII) required as starting materials for carrying out the process step 4) according to the invention are known (cf. Giannella; Pigini, FRPSAX, Farmaco Ed.Sci., 28, 1973, 157,159), and they are obtained by a novel route according to process step 7) from compounds of the formula (IV), or according to process step 3) from compounds of the formula (VI).
On the one hand, the compounds of the formula (VI) required as starting materials for carrying out the known process step 5) are known and can be prepared by processes known per se, on the other hand, they are obtained by a novel route according to process step 2).
The compounds of the formula (IV) required as starting materials for carrying out the process step 3) according to the invention have already been described in the description of the process step 5).
The starting materials of the formula (X) used in process step 8) in which R1, R2, R3 and R4 represent hydrogen and R5 represents methyl are mentioned by name in EP-398692, the starting materials of the formula (X), used in process step 8) in which R1, R2, R3 and R4 represent hydrogen and R5 represents alkyl are described under formula (VIII) on page 8 and page 14 and page 36 in WO9746542. They are also described under formula (IV) on page 7 and 8 and on pages 17, 19 and 20 in EP-846691.
The starting materials of the formula (II) used for carrying out the process step 1) can be prepared by process part 1Aa), process part 1Ab), process part 1B, process part 1C or by process part 1D by carrying out the process steps successively or by a one-pot process.
The starting materials used for carrying out the process steps 9), 10) and 11) are described in WO 98/21189.
The compounds of the formula (XI) used for carrying out the isomerization are obtained according to process part 1 and part 2.
All other starting materials are customary commercial products or can be prepared from these by simple processes.
Process step 2 is novel and also forms part of the subject-matter of the invention.
The process step 3) according to the invention yields the compounds of the formula (VII). The compounds of the formula (VII) are novel and inventive and form part of the subject-matter of the invention, except for the compounds of the formula (VII-a) 
The process step 7) according to the invention yields the compounds of the formula (VII). The compounds of the formula (VII) are novel and inventive and form part of the subject-matter of the invention.
With the aid of the entire process (process part 1 and process part 2), the preparation of the known pesticides of the formula (XI) (cf. WO 98/21189) is considerably improved and simplified.
The process part 1 according to the invention serves to prepare important intermediates of the formula (I) and gives these intermediates a high and improved yield.
In process part 2 according to the invention, too, an increased yield in comparison to known processes can be observed.
By carrying out the isomerization after process part 2, in particular after process steps 10 and 11, the proportion of the E isomer in the isomer mixture is increased.